It was well past midnight and Mitt Romney wanted to talk. The political scion had traveled from Boston to Washington for an event at which he hoped to meet then-President Ronald Reagan, but a sudden cancellation relegated his tuxedo to his Marriott hotel room. With the White House just down the block, Romney confided to a Bain and Co. colleague the trajectory sketched out for him by his father.

“Dad says, first you go into business and you make a lot of money, you give the church half of it, and then you go into public service,” Romney said, according to his Bain colleague and Marriott roommate Patrick Graham. “And then you become president of the United States.”

Romney has followed his father’s road map. By the early 1990s, he had matured from his days as a privileged youth to build a family, a fortune, and a flock as the leader of his church in the Boston area. He also grew receptive to encouragement from family members and others who considered him born and bred to replace less-perfect men in power. They wanted Romney to take on Ted Kennedy in 1994.

Romney’s decision to become a candidate set him out on a path riddled with bumps and detours, ideological turns, successes that veered him toward Washington and failures that knocked him off track. Along the way, Romney has demonstrated that the cardinal directions on his compass do not indicate a political left or right. The true north he has relentlessly pursued is a personal success measured by the approval of others. The fulfillment of dreams from his father — a former Michigan governor and would-be president — and the political destiny invoked by his wife, Ann, intensified Romney’s ambition.

As a fledgling candidate for the Senate, Romney prepared for his race against Kennedy by demonstrating elasticity on key positions. He showed a reluctance to discuss his religion, a reliance on fundraising brawn to intimidate potential opponents and a tendency to appeal to arbiters when placed under pressure. It was a contest that he told some family members he never thought he would win. But when he had a shot at winning he failed to listen to his gut — and his father — to beat back attacks on his business record. He blamed his loss on the tactics of his campaign staff, the bias of the media and the electorate’s inability to appreciate what he had to offer. He then retreated to the places where he felt most at home — business, family, the church.

“He thought it was done,” said Tagg Romney, his oldest son. “We all did.”

But Romney came back, again and again and again, leading to his current uncharted moment. It is a final stretch that much resembles his first cautious step into the political arena.

GOP’s state of ‘disaster’

There was no obvious on-ramp into Republican Massachusetts politics in the 1980s. The party had been relegated to irrelevance, and the candidates left something to be desired. In the 1986 race for governor, one Republican candidate who claimed to have served in Vietnam had only visited the country. Another had a reputation for working nude in his office. The party’s ultimate nominee was a write-in candidate.

“1986 was a disaster,” said Paul ­Cellucci, a Republican state legislator who later became governor.

Over the next months and years, as the party’s new leadership sought to rebuild, Romney first flashed on the radar as a fundraiser and a potential talent. But for Romney, the timing was not right. It was 1988, and the Massachusetts miracle was in full swing. The state’s governor, Michael Dukakis, was the Democratic nominee for president. The state Republican Party chairman, Ray Shamie, hired a pollster to gauge his own chances against Kennedy. The survey said? Unbeatable. Shamie and his executive director, Joe Malone, combed national fundraising lists for potential candidates among Massachusetts residents. Bain executives appeared frequently, including Romney’s friend Graham, who had declined several invitations to run for office.

“Look, guys. I’m so embarrassed. Every two years I keep saying, ‘No, no, no,’ ” Graham recalled telling the party bosses during one meeting at Boston’s Union League Club. “But I’m bringing you a possible candidate.”

Romney had stayed safely on the margins of politics, but his pedigree, good looks and, most significant, personal wealth increasingly caught the eye of other Republican leaders. Cellucci, who served as George H.W. Bush’s Massachusetts campaign chairman, met with Romney and thought he “had some personal wealth that could get him off the ground.” When Romney finally met Shamie and Malone at the Copley Plaza hotel, across the street from Romney’s then-thriving investment offshoot, Bain Capital, they asked him if he would like to join the Key Club, a group of top-level fundraisers. Romney responded that he would write a check from time to time, Malone recalled, but that he was not ready for such a commitment at that moment.

As the men stood up to leave, Malone said to Romney, “Have you ever thought about running for office?”

“Why do you ask?” Romney said.

“Well, with your background, and the presence that you have,” answered Malone, who ran as a sacrificial lamb against Kennedy that year, “I think you would be a perfect candidate.”

The Romney campaign declined to comment for this article.

Republican inroads

By 1990, momentum had begun to build behind the Republican message of reinventing government. For the first time since the early 1970s, Republicans had won statewide office. Bill Weld clinched the governorship, Cellucci became lieutenant governor and Malone took office as state treasurer. Republicans won more than a dozen seats in the state legislature. The wave continued in 1992, when two Republicans, including Peter Blute, won seats in Congress.

Blute recalled going to Romney’s modest office at Bain after his victory and hitting Romney up for a donation. By then, Blute said, Romney was known as a “big wheel.” The two discussed general economic issues and what Blute called their “moderate conservative” outlook. “He was happy that we had won and broken through the total dominance of Democrats,” Blute recalled. “You could tell he was interested in politics at that time.”

Romney had grown up steeped in campaign rallies and victory parties. He had also seen the pain politics could cause. George Romney’s trouncing in the presidential campaign of 1968, followed by the defeat of Mitt’s mother, Lenore, in a race for Michigan’s U.S. Senate seat, deeply disappointed Romney, according to his son Tagg. But a quarter-century had passed to heal those wounds.

In addition to Romney’s father’s words weighing on him, Romney also now had the dying wishes of his wife’s father to consider. In a period of emotional upheaval for Romney’s family in which Ann suffered a miscarriage, her father, Edward Roderick Davies, fell ill with cancer. More skeptical of organized religion than his children, who had been converted to Mormonism by the Romneys, Davies beseeched his daughter to make the most of her life now, and to capi­tal­ize on the opportunities bestowed upon her and her husband, Ann told the Boston Globe. In September 1992, Davies died, and months later Romney accompanied his brothers-in-law to a Mormon temple, where, donning white robes, he solemnly watched as they posthumously baptized their father through a proxy, according to a person present at the ceremony.

In the Romneys’ telling, it was this personal loss that put their lives in perspective.

“I thought, ‘Mitt, are we going to die someday and then say, Mitt, you never did it! You never tried?’ That’s why Mitt’s running,” Ann said. Widespread reports that depicted Kennedy as a man of sloth, gluttony and alleged infidelities provided an impetus for Romney’s candidacy.

This version glosses over the basic political calibration of an ambitious man sensing and seizing his opportunity. But while George Romney proscribed the political formula by which Mitt Romney has led his life, friends and even some closely placed detractors of Romney say Ann, with a strong sense of her husband’s political pedigree and destiny, was the enzyme.

“She insisted he go out and take on the Olympics,” said Mitt’s sister Jane Romney. Years later, during her husband’s first presidential campaign, Ann told a family friend and fellow Mormon, Dennis King, that Mitt’s running was something “God wanted him to do.”

After his defeat, Romney sought to step back and bow out of the 2012 race, according to son Tagg. “We had to convince him hard to run, my mom and I,” he said. “I know some people don’t believe us.”

At the time of her husband’s first foray into electoral politics, Ann recounted how she had turned to Romney in bed one morning in the summer of 1993, frustrated by her husband’s grousing about Kennedy’s poor example, and with her father’s advice fresh in mind.

“If you don’t stand up and do something about it, then, you know, shut up and stop bothering me,” she said, according to “The Real Romney,” a biography by two Globe reporters.

Romney pulled the covers over his head.

“No!” he said. “No! I don’t want to do it.”

Obligations

Led by duty, pushed by family, or spurred by his own ambition, it fell to Romney to take the first step. And to complete the journey, he needed to unload all the unnecessary baggage possible, taking a leave from Bain and seeking a premature release from his church obligations.

When George Romney, the highest Mormon authority in Detroit as stake president, considered running for governor decades earlier, he sought the counsel of David O. McKay, then the president of the Church of Jesus Christ of Latter-day Saints. Mitt Romney, having followed in his father’s footsteps by becoming the Boston stake president in 1986, also needed to consult a higher authority. The office’s term usually lasted about nine years, and Romney appealed to his church’s leaders for an exemption from service. According to Gordon Williams, Romney’s mentor and predecessor as stake president, the burgeoning politician expressed concern to the church hierarchy in Salt Lake City that the church would be tainted with politics if he maintained his official position while running. The church agreed, and freed him up in March 1994.

Yet Romney’s connections in the church proved critical at the inception of his political career. Months before the hierarchy released him from his obligations as Boston’s highest church authority, Romney called Richard Bitner Wirthlin, Reagan’s chief strategist and pollster, who had become a high-ranking church official in Salt Lake City.

“They counseled together early on,” recalled Jeralie Wirthlin, the pollster’s widow, who said Romney visited her husband in their Utah home.

Richard Wirthlin showed Romney polling that made clear that no candidate opposed to Roe v. Wade had a prayer of getting elected statewide in Massachusetts, according to Ron Scott, Romney’s former communications specialist in the Boston stake and a Romney biographer. Scott said Romney told him of the polling and a trip Romney made to Salt Lake City with Wirthlin, whose half first cousin was the church’s president, Gordon Bitner Hinckley.

“I left a few bridges burning, or at least smoldering,” Romney said of the trip, according to Scott. Romney had shown the members of the hierarchy Wirthlin’s polling, Scott said, but also made the case that the church’s doctrine of free agency emphasized personal choice and provided cover for a pro-abortion-rights position.

In an October 1993 telephone call to Scott, Romney, who had switched his party affiliation from independent to Republican, revealed his intentions to run. Romney then asked Scott, a former reporter, what issues he would probably face in such a race.

“Mormonism,” Scott responded.

“Why should that be an issue?” Romney asked.

“Well, that’s not the question you asked me,” Scott answered.

Scott suggested a media strategy in which Romney would immunize himself from any potential anti-Mormon attacks by using his famous name to attract national media attention. Those broader stories would be more forgiving than ones in the hometown papers, and they would allow Romney to both define himself and better acquaint the country with his faith and history. Romney rejected the suggestion. At the end of the call, he asked Scott for an assessment of his chances.

“It’s possible,” Scott said of a Romney victory, adding that he also saw little downside in a respectable defeat. “No one is going to fault you for that, because you are taking on the most formidable politician in America, and you will be positioned for whatever you want to in the future.”

The campaign team

Romney now needed to put a team together. In the fall of 1993, Romney had signed the Wirthlin Group to do his polling. He acquired as a media guru Greg Stevens, a hot commodity for his production of the famous 1988 spot lampooning a helmeted Dukakis driving a tank. As his campaign manager he hired away Blute’s chief of staff, a well-connected former legislator named Robert Marsh, who in turn recruited staff from statehouse offices and introduced Romney to the new party chairman, Leon Lombardi. For senior strategist, Romney hired Charley Manning, a Weld veteran. Manning then placed calls to the party’s power brokers informing them that Romney was for real. Then Romney called.

“I’m not kidding myself. I know it’s going to be an uphill fight,” Romney told Malone, who characterized the call as an attempt to nail down his support early. “If I do this, I’m going to need your help.” Malone responded that he and the other party leaders preferred a wait-and-see approach.

At the start, Romney focused on better-known candidates, including Janet Jeghelian. Jeghelian had the advantage of being a woman in an election defined in part by Kennedy’s apparent philandering, and she had significant name recognition from her years as a morning radio talk-show host. As the field took shape, Romney asked her to meet with him at a Boston hotel, where he told her he planned to “go all out, 100 percent with this effort,” Jeghelian recalled. “That meant he would raise as much money as necessary to win.”

Romney’s main rival for the Republican nomination proved to be John Lakian, a fellow investor with some political baggage. Lakian’s 1982 bid for governor was marred when the Boston Globe reported that he had lied about having attended graduate school at Harvard University, embellished his war record and incorrectly said in campaign literature that his father died of war-related injuries. (Lakian’s father died after being hit by a trolley.)

As the race got underway, Romney met Lakian for lunch at a downtown Boston hotel and made the case that the Cape Cod resident would get a higher return on investment if he ran for the House of Representatives.

“Why be competitive when it’s going to be difficult enough to beat Ted Kennedy,” Romney said, according to Lakian, who added that in retrospect, Romney was right and it was a “lopsided race.” Instead, Lakian stuck it out and campaigned around the state against Romney.

Mitt was not the only Romney on the trail. At Republican town committees around the commonwealth, Romney’s father, George, proved a constant presence. “He was out there every night, and I had the feeling he was probably critiquing him on every performance,” Jeghelian said.

Campaign aides at the time said the elder Romney sometimes seemed to appear out of thin air. He would fly in alone from Detroit, take the shuttle to the subway, ride the Red Line out to the last stop, Alewife Station, and then wheel his suitcase behind him for a 45-minute walk along the expressway, over an overpass, beside the Cambridge reservoir and through an office park where, at the end of the road, he would climb three flights of stairs up to campaign headquarters at 68 Moulton St.

“Oh, Dad, you’re here,” Romney would say.

Romney welcomed his father’s assistance. In his Belmont home, he and Ann put a treadmill in the guest room so George could walk an hour every morning before meeting everyone in the kitchen at 6 a.m., bursting with ideas.

Of major concern to the father was countering the simmering talk about his son’s faith. According to Jeghelian, Mormonism was a “sub rosa” issue. “It wasn’t one of those things that was openly talked about but behind the scenes was.” She said that when concerned voters would privately ask her about Romney’s faith, she would say, “What do we even know about Mormonism to even really comment on it?”

During a debate, Lakian accidentally addressed Romney as “Mr. Mormon.” He said Romney did not take offense and was “very square and straight about it.”

Romney wasn’t always so forgiving. As he came under attack from other Republicans in the race for having given money to Democrats in the past, Romney called Jim Rappaport, then the state Republican Party chairman, to complain.

“Well, you did give checks to Democrats, didn’t you?” Rappaport said.

“Well, yeah,” Romney countered, according to Rappaport. “But you’ve given checks to Democrats.”

“No,” Rappaport said. “Never in a contested race.”

In February 1994, Romney appeared on the radio show of Dan Yorke and lamented the late primary date. In a move that foreshadowed his initial strategy during the 2012 primaries, he urged his opponents to “focus on Ted Kennedy instead of focusing on one another.” He also steered clear of the abortion issue, saying, “Abortion’s the law of the land, I wouldn’t change it,” and adding, “My church does not take a view on whether politically you should legislate that or not.”

Romney also exalted his political pedigree.

“Dad was governor, ran for president,” Romney said. “Mom ran for U.S. senator.”

“All right, so it’s in the blood,” Yorke suggested.

“It’s in the blood,” Romney said.

Primary win

Romney did everything he could to cut the primary short and focus his time, energy and money on Kennedy. At the May convention, Romney won 68 percent of the delegate votes. Lakian won 16 percent, just enough to force a Sept. 20 primary ballot. The result soured Romney’s first taste of electoral victory.

Establishment party figures, including Ron Kaufman, argued that the primary challenge would make Romney a better candidate. To better keep Romney on track, the campaign decided to bring on Bob White, a Bain colleague who remains Romney’s closest confidant.

As Romney continued to battle Lakian, the Kennedy campaign prepared for Romney.

“We had not heard of him,” said Scott Ferson, who worked in the Kennedy press shop. But when it became clear that Romney would be their opponent, Kennedy opposition researchers made trips to the Boston Public Library and leafed through old bound Securities and Exchange Commission filings. Their break came out of the blue, when a representative of disgruntled workers at the Bain-owned American Pen & Paper (Ampad) in Indiana got through to the research director.

Romney crushed Lakian in the primary, 83 percent to 17 percent. The celebration was short-lived. Almost immediately, the Kennedy campaign aired a brutal television ad featuring the grievances of the Ampad workers.

According to one campaign staffer, George Romney immediately sensed that the ads had struck a chord with Massachusetts voters and insisted that his son counterattack. Romney seemed to agree, but Stevens, his professional media adviser in Washington, counseled against prematurely spending money on defensive ads, according to one aide at the time.

Romney sided against his father, who continued to protest.

“I get it, Dad!” Romney responded.

‘Mitt comes back’

Kennedy overwhelmed Romney. Surrounded by his father and much of his family for a reunion only days after the election, he did his best to put on a brave face. Romney’s son Tagg and his sister Jane recalled how he laid on his back in the center of a room, closing his eyes and clutching a bouquet of lilies above his chest. The joke, according to another person in the room, was that Romney knew he was “dead and buried.”

But the loss hurt. Not long afterward, Romney invited Malone, the state’s treasurer, out to dinner for what Malone called a “postmortem.” As the two men sat across from each other with their wives at the Tuscan Grill in Waltham, they began by discussing their holiday plans and the Christmas bonuses Romney had given to his Bain employees. Then Ann expressed her disbelief in his loss, and her supreme confidence in her husband’s abilities.

Romney took the cue and complained that he had built a campaign team so quickly that he was forced, in essence, to “dance with the one who brought him,” Malone recalled. He expressed disappointment that the voters had not understood what he was about and blamed his failure not on his philosophy, or the unpopularity of the issues he championed, but, according to Malone, that “tactically they had missed the boat.”

Romney also blamed the media. James Cannon, who, like Romney, had served as bishop of the church’s Cambridge ward, met with Romney soon after the loss and asked what lessons he had learned.

“I learned the power of the Kennedy name,” Romney responded, according to Cannon. “Because once they got serious, the press just turned against us.”

The loss chastened Romney and temporarily discouraged him from other bids. In 1996, a year after George Romney’s death, Weld drove out to Mitt’s house and offered him first dibs at that year’s race against Democratic Sen. John F. Kerry. Weld said that Romney answered the door and apologized for not having any Jack Daniels in the house and that then the two men “rapidly established that he had no interest” in the office. “He and Ann didn’t want any part of that.”

Eventually, Romney looked for alternative paths to achieve his father’s dream for him.

“That’s probably the definitive quality he has, picking up the pieces and making the best of it and going forward,” Jane Romney said. “Losses are discouraging and hard, but Mitt comes back.”

In 1999, the year he took the job chairing the Salt Lake City Olympics, the position that put his public service career back on track, Romney and other prominent Mormons worked to get local approval for a landmark Mormon temple in Belmont. Ferson, Kennedy’s former operative, came on to help in the effort and one day found himself listening to Romney, the past and future candidate, waxing wise about the local Belmont politics.

“You know, I’ve got some experience in politics,” Romney joked, according to Ferson. “It’s interesting that when you come in you can’t really control the landscape and the way people react to you.”

Ferson said he felt uncomfortable because Romney clearly did not know his background with Kennedy. He interrupted Romney. “I’m familiar with that race,” he said. “I used to work for Senator Kennedy.”

Ferson said Romney paused and smiled. “Well,” Romney said. “You did a good job.”